Methylglyoxal → Quinoxaline

HRID 1375305Notes

Reaction equation

HRID 1375305 reaction equation
C(C=O)=O.CC(C=O)=O.[CH2:10]([C:17]([CH:19]=O)=O)[C@H:11](O)[C@H:12](O)[CH2:13]O.Cl(O)(=O)(=O)=O.[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32]>CC(=O)C(=O)C>[N:32]1[C:12]2[C:11](=[CH:10][CH:17]=[CH:19][CH:13]=2)[N:33]=[CH:26][CH:27]=1.[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32]

Participants

8

Reactant 5

HCID 880MethylglyoxalHCID 7243O-PhenylenediamineHCID 7860GlyoxalHCID 24247Perchloric AcidHCID 1148393-Deoxyglucosone

Product 2

HCID 7045QuinoxalineHCID 7243O-Phenylenediamine

Reagents, catalysts & solvents 1

HCID 650ButanedioneSolvent

Procedure

The quantities of residual glyoxal, methylglyoxal, and 3-deoxyglucosone in the sample solution were determined by high-performance liquid chromatography (HPLC) following the incubation. More specifically, 40 μl of 2M perchloric acid, 40 μl of 1% o-phenylenediamine, and 100 μl of 25 μM 2,3-butanedione were added to 100 μl of the sample after the incubation; the mixture was stirred and incubated at 25° C. for 1 hour. Quinoxaline derivatives produced in the reaction of the dicarbonyl compounds and o-phenylenediamine were quantified by HPLC using a reverse-phase column according to the method of Ohmori et al. (Ohmori S. et al., J. Chromatogr. 414: 149–155,1987). Glyoxal, methylglyoxal, and 3-deoxyglucosone were used as standard samples.

Sources & evidence

ORD record
ord-eafb8e2f870947869aa998473a3afabb
Source dataset
uspto-grants-2007_01
Patent number
US07169407B1

Reaction notes

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